HCID 20196477, compound → HCID 20196470, compound

HRID 652732Notes

Reaction equation

HRID 652732 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[N:4][CH2:3]1>C1C2C(CCCC2)CCC1.[Pd]>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 20196477HCID 20196477, compound

Product 1

HCID 20196470HCID 20196470, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7044DecalinSolvent

Procedure

A mixture of 3,4-dihydro-4-methyl-7-nitroisoquinoline (14.63 g) and palladium black (4 g) in decahydronaphthalene (170 ml) was refluxed for 6 hours with stirring. The reaction mixture was allowed to stand overnight at ambient temperature, and then filtered and the residue on a filter was washed with chloroform. The filtrate was extracted with 2N hydrochloric acid (70 ml×3). Aqueous sodium hydroxide was added slowly to the combined aqueous layer, under dryice-acetone cooling. The light brown solid was collected, washed with water and dried. The crude product was chromatographed on silica gel column using chloroform as an eluent to give 4-methyl-7-nitroisoquinoline (6.06 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationfiltered
  3. washthe residue on a filter was washed with chloroform
  4. extractionThe filtrate was extracted with 2N hydrochloric acid (70 ml×3)
  5. additionAqueous sodium hydroxide was added slowly to the combined aqueous layer, under dryice-acetone cooling
  6. customThe light brown solid was collected
  7. washwashed with water
  8. customdried
  9. customThe crude product was chromatographed on silica gel column

Sources & evidence

ORD record
ord-444ba82cb3714198ad1d510e86fa6d60
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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